%0 Journal Article
%A Maezaki, Naoyoshi
%A Yuyama, Sachiko
%A Sawamoto, Hiroaki
%A Suzuki, Tomoko
%A Izumi, Mayuko
%A Tanaka, Tetsuaki
%D 2000
%T Highly Stereoselective Intramolecular
Michael Addition Using α-Sulfinyl
Vinyllithium as an Unprecedented
Michael Donor
%U https://acs.figshare.com/articles/journal_contribution/Highly_Stereoselective_Intramolecular_Michael_Addition_Using_-Sulfinyl_Vinyllithium_as_an_Unprecedented_Michael_Donor/3737550
%R 10.1021/ol006697a.s001
%2 https://ndownloader.figshare.com/files/5829318
%K Stereoselective Intramolecular Michael Addition
%K Michael adducts
%K Michael addition
%K intramolecular Michael addition reaction
%K cyclopentene ring formation
%K Michael donor
%K stereogenic center
%K Unprecedented Michael Donor
%X The first example of an asymmetric intramolecular Michael addition reaction using α-lithiated vinylic sulfoxide as a Michael donor is reported.
Michael addition of the α-lithiated vinylic sulfoxide to (Z)-enoates proceeds with high diastereoselectivity to give the adducts having a stereogenic
center with (R)-configuration at the β-position of the ester in the cyclopentene ring formation. The selectivity was reversed in the six-membered
ring formation. On the other hand, the corresponding (E)-enoates provided Michael adducts with poor diastereoselectivity.
%I ACS Publications